Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents

被引：106

作者：

Chierchia, Matteo ^{[1
]}

Xu, Peilin ^{[1
]}

Lovinger, Gabriel J. ^{[1
]}

Morken, James P. ^{[1
]}

机构：

[1] Boston Coll, Dept Chem, 2609 Beacon St, Chestnut Hill, MA 02467 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 40期

关键词：

boron; catalysis; cross-coupling; nickel; radical reactions; CATALYZED INTERMOLECULAR TRIFLUOROMETHYLARYLATION; POLAR CROSSOVER REACTIONS; REDUCTIVE DICARBOFUNCTIONALIZATION; UNACTIVATED OLEFINS; HALIDES; CYCLIZATION; STYRENES; ESTERS; 1,2-DIFUNCTIONALIZATION; DIFUNCTIONALIZATION;

D O I：

10.1002/anie.201908029

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A hybrid transition-metal/radical process is described that results in the addition of organozinc reagents and alkyl halides across alkenyl boron reagents in an enantioselective catalytic fashion. The reaction can be accomplished both intermolecularly and intramolecularly, providing useful product yields and high enantioselectivities in both manifolds.

引用

页码：14245 / 14249

页数：5

共 102 条

[11] Asymmetric Synthesis of Secondary and Tertiary Boronic Esters [J].

Collins, Beatrice S. L. ;

Wilson, Claire M. ;

Myers, Eddie L. ;

Aggarwal, Varinder K. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (39) :11700-11733

[12] Catalytic Enantioselective Cyclization/Cross-Coupling with Alkyl Electrophiles [J].

Cong, Huan ;

Fu, Gregory C. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (10) :3788-3791

[13]

Curran D.P., 1996, Stereochemistry of Radical Reactions

[14] Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides [J].

Derosa, Joseph ;

Kleinmans, Roman ;

Tran, Van T. ;

Karunananda, Malkanthi K. ;

Wisniewski, Steven R. ;

Eastgate, Martin D. ;

Engle, Keary M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (51) :17878-17883

[15] Directed nickel-catalyzed 1,2-dialkylation of alkenyl carbonyl compounds [J].

Derosa, Joseph ;

van der Puyl, Vincent A. ;

Tran, Van T. ;

Liu, Mingyu ;

Engle, Keary M. .

CHEMICAL SCIENCE, 2018, 9 (23) :5278-5283

[16] Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling [J].

Derosa, Joseph ;

Tran, Van T. ;

Boulous, Mark N. ;

Chen, Jason S. ;

Engle, Keary M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (31) :10657-10660

[17] Transition Metal-Catalyzed Dicarbofunctionalization of Unactivated Olefins [J].

Dhungana, Roshan K. ;

Shekhar, K. C. ;

Basnet, Prakash ;

Giri, Ramesh .

CHEMICAL RECORD, 2018, 18 (09) :1314-1340

[18] Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents [J].

Edelstein, Emma K. ;

Namirembe, Sheila ;

Morken, James P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (14) :5027-5030

[19]

Fernández E, 2015, TOP ORGANOMETAL CHEM, V49, pV

[20] Lithium Organozincate Complexes LiRZnX2: Common Species in Organozinc Chemistry [J].

Fleckenstein, Julia E. ;

Koszinowski, Konrad .

ORGANOMETALLICS, 2011, 30 (18) :5018-5026

← 1 2 3 4 5 6 7 8 9 10 →